Winnetka Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Winnetka vacation rentals

Game room
Relaxing Getaway w/ Game Room, Pickleball & More

Vacation Home in Canoga Park

Relaxing Getaway w/ Game Room, Pickleball & More
10.0 out of 10, Exceptional, (3)
"Host was very responsive. Lovely, very clean home. We stayed for a week for Thanksgiving. Convenient to shops and restaurants. Would definitely stay again. "
United States
Lisa F.
The price is ￥30,907
￥98,624 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Relaxing Getaway w/ Game Room, Pickleball & More
Marina
Cozy good vibes boat experience in Marina Del Rey. Perfect location in safe area

Houseboat in Marina del Rey

Cozy good vibes boat experience in Marina Del Rey. Perfect location in safe area
8.8 out of 10, Excellent, (50)
"Great location, great host, fun little get away!"
United States
vickey m.
The price is ￥16,510
￥24,276 total
includes taxes & fees
Dec 30 - Dec 31
Cozy good vibes boat experience in Marina Del Rey. Perfect location in safe area
Exterior detail
Luxury Covered Wagon in Santa Monica Mountains close to Malibu w/ King Bed

Mobile Home in Westlake Village

Luxury Covered Wagon in Santa Monica Mountains close to Malibu w/ King Bed
10.0 out of 10, Exceptional, (9)
"Our whole family loved staying here. Despite this being a glamping spot, the inside of the wagon and the bathroom were very clean. "
United States
Olga C.
The price is ￥31,314
￥46,032 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Luxury Covered Wagon in Santa Monica Mountains close to Malibu w/ King Bed
Dining room
Gilmore One

Aparthotel in Van Nuys

Gilmore One
4.0 star property
8.6 out of 10, Excellent, (124)
"Everything was awsome, The bulding was clean and spotless..... My secound time staying here highly recommended "
Canada
ISKANDAR
The price is ￥12,436
￥23,102 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Gilmore One
Terrace/patio
Fabulous guest house just minutes away from anything you would need!

Cottage in Grandview

Fabulous guest house just minutes away from anything you would need!
9.8 out of 10, Exceptional, (55)
"Great house in a great neighborhood! This place checks all the boxes! "
United States
Rich D.
The price is ￥21,568
￥37,582 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Fabulous guest house just minutes away from anything you would need!
Pool
Brand New Charming Guest House in lovely Northwest Glendale CA. Private &Quiet

Cottage in Brockmont

Brand New Charming Guest House in lovely Northwest Glendale CA. Private &Quiet
10.0 out of 10, Exceptional, (5)
"Nice quiet getaway place. The place was very clean. The location is in a beautiful neighborhood surrounded by beautiful landscaping. The interior decor was aesthetically pleasing. Me and my partner will be coming back to this place when we travel to LA. The bedding was very comfortable and relaxing. The jacuzzi hot tub provided that added comfort after a long day out. Thank you for providing added memories to our life."
United States
Willie S.
The price is ￥27,965
￥49,200 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Brand New Charming Guest House in lovely Northwest Glendale CA. Private &Quiet
Apartment | 1 bedroom
Scenic Retreat With Deck Stunning Views in LA

Vacation Home in Atwater Village

Scenic Retreat With Deck Stunning Views in LA
2.0 star property
10.0 out of 10, Exceptional, (3)
"Good"
United States
Shantinique
The price is ￥26,144
￥48,221 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Scenic Retreat With Deck Stunning Views in LA
Exterior detail
*Self check-in. Private Entrance. Netflix.*

Vacation Home in West Hills

*Self check-in. Private Entrance. Netflix.*
9.2 out of 10, Wonderful, (17)
"GREAT stay! Quaint, cozy room/bathroom that had everything I needed. Excellent location! Owner very responsive! "
United States
Yvette F.
The price is ￥12,803
￥33,026 total
includes taxes & fees
Jan 1 - Jan 2, 2026
*Self check-in. Private Entrance. Netflix.*
Interior
Charming stand alone guest house in Burbank close to universal studios

Vacation Home in Burbank

Charming stand alone guest house in Burbank close to universal studios
10.0 out of 10, Exceptional, (5)
The price is ￥18,632
￥38,203 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Charming stand alone guest house in Burbank close to universal studios
Pool
View Park Angeles with Private Pool

Apartment in View Park-Windsor Hills

View Park Angeles with Private Pool
9.8 out of 10, Exceptional, (7)
"Really enjoyed our stay. Location was perfect for us. Had a great time. Easy check in process. Everything was as described. Unfortunately it was too cool to use the pool but will be back again. "
United States
Deb G.
The price is ￥19,023
￥35,619 total
includes taxes & fees
Jan 5 - Jan 6, 2026
View Park Angeles with Private Pool
Interior
Mermaid Suite + Private Trails, Cave and Creek!

Vacation Home in Topanga

Mermaid Suite + Private Trails, Cave and Creek!
8.6 out of 10, Excellent, (7)
"Wonder place to stay to get out of the city for a great price… would definitely stay again. "
United States
Douglas W.
The price is ￥17,175
￥25,763 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Mermaid Suite + Private Trails, Cave and Creek!
Exterior
Topanga Japanese Tea House + Private Creek + Mountain Trails.

Cabin in Topanga

Topanga Japanese Tea House + Private Creek + Mountain Trails.
9.0 out of 10, Wonderful, (47)
"We really enjoyed our stay here at the Japanese Tea House! We would love to have the opportunity to stay here again. "
United States
natalie c.
The price is ￥19,518
￥28,262 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Topanga Japanese Tea House + Private Creek + Mountain Trails.
Terrace/patio
"The Best" Jacuzzi View Private Luxury Guest Cottage-Better than a Room or Suite

Cottage in Thousand Oaks

"The Best" Jacuzzi View Private Luxury Guest Cottage-Better than a Room or Suite
2.5 star property
10.0 out of 10, Exceptional, (33)
"Great place "
United States
Gary S.
The price is ￥31,228
￥54,649 total
includes taxes & fees
Jan 2 - Jan 3, 2026
"The Best" Jacuzzi View Private Luxury Guest Cottage-Better than a Room or Suite
Fridge, microwave, oven, stovetop
Cozy Family Hideaway, sleeps 8, yard, hikes, shops, 30 mins to beach

Vacation Home in Santa Susana

Cozy Family Hideaway, sleeps 8, yard, hikes, shops, 30 mins to beach
9.8 out of 10, Exceptional, (30)
"Spacious and well-stocked, this was a convenient place for us to stay as a family"
United States
Connor G.
The price is ￥18,128
￥49,312 total
includes taxes & fees
Dec 30 - Dec 31
Cozy Family Hideaway, sleeps 8, yard, hikes, shops, 30 mins to beach
Fridge, microwave, oven, stovetop
This apartment is a 2 bedroom(s), 2 bathrooms, located in Santa Clarita, CA.

Apartment in Santa Clarita

This apartment is a 2 bedroom(s), 2 bathrooms, located in Santa Clarita, CA.
10.0 out of 10, Exceptional, (12)
"Really nice, safe property. Close to restaurants, stores and the park. "
United States
Lara S.
The price is ￥21,552
￥51,531 total
includes taxes & fees
Jan 6 - Jan 7, 2026
This apartment is a 2 bedroom(s), 2 bathrooms, located in Santa Clarita, CA.
Exterior
Beautiful 1972 Classic Airstream in Santa Monica Mountains

Vacation Home in Thousand Oaks

Beautiful 1972 Classic Airstream in Santa Monica Mountains
8.8 out of 10, Excellent, (34)
"Excellent Santa Monica mountain's location Meggan and her husband provided excellent directions and instructions. Great place to stay, wish I had more time to spend there."
United States
Patrick D.
The price is ￥19,244
￥32,672 total
includes taxes & fees
Dec 29 - Dec 30
Beautiful 1972 Classic Airstream in Santa Monica Mountains
Exterior
Remodeled Stylish Culver Cottage + Parking

Cottage in Carlson Park

Remodeled Stylish Culver Cottage + Parking
10.0 out of 10, Exceptional, (86)
"Cute place ! Everything you need in the unit or within walking distance "
United States
Joshua H.
The price is ￥24,112
￥49,454 total
includes taxes & fees
Dec 28 - Dec 29
Remodeled Stylish Culver Cottage + Parking
House, 1 Queen Bed, Patio, Mountain View (1733 Los Angeles) | Living area | 42-inch flat-screen TV with digital channels
Scenic Retreat With Deck & Stunning Views in LA

Vacation Home in Atwater Village

Scenic Retreat With Deck & Stunning Views in LA
3.5 star property
The price is ￥24,640
￥96,488 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Scenic Retreat With Deck & Stunning Views in LA
Beach
Cozy Home W/Pool & GYM + Parking 10min to Cedars

Apartment in Mid-Wilshire

Cozy Home W/Pool & GYM + Parking 10min to Cedars
9.0 out of 10, Wonderful, (6)
"Fantastic, central location. Parking included. Fabulous amenities. Responsive owners. We will definitely attempt to stay here again next time we’re in LA. "
United States
John G.
The price is ￥18,425
￥49,528 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Cozy Home W/Pool & GYM + Parking 10min to Cedars
Exterior
Remodeled Designer Cottage with Bicycles

Vacation Home in Carlson Park

Remodeled Designer Cottage with Bicycles
10.0 out of 10, Exceptional, (89)
"Overall great stay. Easy to get in and out, easy communication, great location."
United States
Edgar C.
The price is ￥22,828
￥47,834 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Remodeled Designer Cottage with Bicycles
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winnetka Hotel Reviews

The Garland

The Garland

10/10 Excellent
"Everything was great "
lisamarie 1-night trip
Posted 13 hours ago
The Garland

Find out more about Winnetka

Search for holiday rentals in Winnetka on Expedia! You can easily find your home rentals, villas, holiday apartments in Winnetka using one of the methods below:

  • View our selection of featured holiday rentals in Winnetka
  • Use the map to find apartments and other holiday homes in the Winnetka neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winnetka while they last

Look no further and take a look at our great range of rental properties in Winnetka!

Frequently asked questions

Are there vacation rentals in Winnetka?

Yes, we have vacation rentals where you'll be only 13.4 mi (21.5 km) from Universal Studios Hollywood, offering you a secluded option if you want a quieter place to stay. Our travelers say Winnetka has a good selection of restaurants. Make sure you have time to check out the shopping and entertainment choices during your trip.

What are some of the best vacation rentals that Winnetka has to offer?

Heart of Hollywood ★ 2 Car Private Parking ★ Walk To Attractions!: This vacation home rental outside of Winnetka is located in the city center and has a fireplace, a balcony, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Winnetka?

Choose from 13 Expedia vacation rentals in Winnetka for a memorable vacation.

What’s there to see and do in Winnetka?

While exploring the area, visit family-friendly sights like Universal Studios Hollywood, or get outside and enjoy nature at Santa Monica Beach. Santa Monica Pier and Six Flags Magic Mountain are other popular places to visit in the area.

What’s a vacation rental in Winnetka like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Winnetka. Vacation rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for families.